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Tandem One-Pot Biocatalytic Oxidation and Wittig Reaction in Water.

ABSTRACT: We explore biocatalytic aldehyde generation under aqueous conditions, concomitantly delivering access to a one-pot Wittig reaction using stabilized phosphoranes and granting diverse alkene products. Using a recombinant choline oxidase mutant, we first undertake biocatalytic alcohol oxidation across a range of functional aliphatic primary alcohols, demonstrating a remarkable substrate tolerance for this enzyme, including chloride, bromide, azide, S-methyl, and alkynyl groups. Following this, we extend capability and deliver a practicable milligram-scale one-pot Wittig reaction in water.

SUBMITTER: Wahart AJC

PROVIDER: S-EPMC11320638 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Tandem One-Pot Biocatalytic Oxidation and Wittig Reaction in Water.

Wahart Alice J C AJC Beardmore Liam N D LND Field Robert A RA Cosgrove Sebastian C SC Miller Gavin J GJ

Organic letters 20240729 31

We explore biocatalytic aldehyde generation under aqueous conditions, concomitantly delivering access to a one-pot Wittig reaction using stabilized phosphoranes and granting diverse alkene products. Using a recombinant choline oxidase mutant, we first undertake biocatalytic alcohol oxidation across a range of functional aliphatic primary alcohols, demonstrating a remarkable substrate tolerance for this enzyme, including chloride, bromide, azide, <i>S</i>-methyl, and alkynyl groups. Following thi ...[more]

PMID: 39075662

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